Potassium tert-butoxide → 6-(4-Bromophenyl)morpholin-3-one

HRID 338413Notes

Reaction equation

HRID 338413 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:15])[CH2:9][NH:10][C:11](=[O:14])[CH2:12]Cl)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][NH:10][C:11](=[O:14])[CH2:12][O:15]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86698749N-(2-(4-bromophenyl)-2-hydroxyethyl)-2-chloroacetamide

Product 1

HCID 778147346-(4-Bromophenyl)morpholin-3-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-(4-bromophenyl)-2-hydroxyethyl)-2-chloroacetamide (2.0 g, 6.8 mmol) in THF (20 mL) was added potassium t-butoxide (0.46 g, 8.2 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was quenched with water (20 mL), extracted with ethyl acetate (20 mL×3). The combined organic layers was dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (1.6 g, 92% yield) as a yellow solid. 1H NMR: (400 MHz, CDCl3): δ7.46 (d, 2H), 7.20 (d, 2H), 6.56 (s, 1H), 4.67 (m, 1H), 4.35 (d, 1H), 4.24 (d, 1H), 3.40 (m, 2H):

Workup

  1. customThe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. dry with materialThe combined organic layers was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a39e2d2efff44beb8a1ae06f4e68d24a
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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